4-Cyano-N-ethyl­spiro­[chromene-2,4′-piperidine]-1′-carboxamide

Rajalakshmi, P.; Srinivasan, N.; Krishnakumar, R.V.

doi:10.1107/S1600536812051124

Volume 69
Part 1
Page o138
January 2013

Received 10 November 2012
Accepted 18 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.050
wR = 0.177
Data-to-parameter ratio = 11.8
Details

4-Cyano-N-ethylspiro[chromene-2,4'-piperidine]-1'-carboxamide

P. Rajalakshmi,^a N. Srinivasan ^a ^* and R. V. Krishnakumar ^a

^aDepartment of Physics, Thiagarajar College, Madurai 625 009, India
Correspondence e-mail: vasan692000@yahoo.co.in

The title compound, C₁₇H₁₉N₃O₂, crystallizes with two independent molecules (A and B) in the asymmetric unit. In both molecules, the pyran ring has a twisted conformation (⁵S₄), with Q = 0.301 (3) Å, [theta] = 116.7 (6) and [varphi] = 213.6 (7)° for molecule A, and Q = 0.364 (2) Å, [theta] = 113.7 (3) and = 213.0 (4)° for molecule B. In molecule B, the terminal ethyl group is disordered over two orientations with an occupancy ratio of 0.55 (1):0.45 (1). In the crystal, molecules A and B form very similar but separate R₁²(7) motifs through N-HO and C-HO hydrogen bonds. The resulting chains along [001] are interlinked by weaker C-HO and C-H [pi] interactions, forming layers parallel to the bc plane.

Related literature

For related structures, see: Rajalakshmi et al. (2012). For their biological activity, see: Kemnitzer et al. (2004); Mahdavi et al. (2011); Patil et al. (2012); Vosooghi et al. (2010). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₇H₁₉N₃O₂
M_r = 297.35
Monoclinic, P 2₁ /c
a = 22.7845 (8) Å
b = 14.3370 (5) Å
c = 9.8442 (3) Å
= 90.783 (1)°
V = 3215.42 (19) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 298 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) T_min = 0.972, T_max = 0.980
26353 measured reflections
5377 independent reflections
3664 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.177
S = 1.04
5377 reflections
455 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.29 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4B-C9B benzene ring

D-HA	D-H	HA	DA	D-HA
N3A-H1N3O2Aⁱ	0.81 (3)	2.12 (3)	2.915 (3)	170 (3)
N3B-H2N3O2Bⁱⁱ	0.83 (2)	2.19 (3)	2.983 (3)	160 (2)
C11A-H11BO2Aⁱ	1.00 (3)	2.27 (3)	3.246 (3)	165 (2)
C11B-H11CO2Bⁱⁱ	0.95 (3)	2.50 (3)	3.344 (3)	147 (2)
C9B-H9BO2Bⁱⁱⁱ	0.92 (3)	2.58 (3)	3.473 (3)	163 (2)
C13A-H13BCg1^iv	0.97	2.91	3.843 (3)	163
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+2, -y+1, -z+2; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLUTON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2085 ).

Acknowledgements

The authors thank the SAIF, IIT, Madras, India, for the X-ray intensity data collection facility.

References

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Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Wang, Y. & Zhao, J. (2004). J. Med. Chem. 47, 6299-6310.
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Patil, D. U., Nikum, P. A., Nagle, S. P. & Mahulikar, P. P. (2012). J. Pharm. Res. 5, 1383-1386.
Rajalakshmi, P., Srinivasan, N. & Krishnakumar, R. V. (2012). Acta Cryst. E68, o2732.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
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organic compounds